Hydrochloric Acid → HCID 86748703, compound

HRID 37631Notes

Reaction equation

HRID 37631 reaction equation
COC([C:5]1([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][C:14]=2[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])=O.Cl>C(O)(=O)C>[CH3:26][C:23]([C:14]1[CH:15]=[C:16]([C:19]([CH3:20])([CH3:21])[CH3:22])[CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][CH:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19936099HCID 19936099, compound

Product 1

HCID 86748703HCID 86748703, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 944 mg (2.74 mmoles) of the title product of Example 12 in 20 ml of acetic acid is added 20 ml of concentrated hydrochloric acid. The mixture is stirred at reflux for 6 hours and then cooled to room temperature. After azeotropic distillation of most of the acetic acid with toluene, water is added and the mixture is extracted first with 50/50 diethyl ether/toluene, and then further extracted twice with toluene. The combined organic extracts are washed with aqueous sodium bicarbonate and then brine, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using mixtures of ethyl acetate and hexane as eluents gives the title compound.

Workup

  1. temperatureat reflux for 6 hours
  2. distillationAfter azeotropic distillation of most of the acetic acid with toluene, water
  3. additionis added
  4. extractionthe mixture is extracted first with 50/50 diethyl ether/toluene
  5. extractionfurther extracted twice with toluene
  6. washThe combined organic extracts are washed with aqueous sodium bicarbonate
  7. dry with materialbrine, dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-b196c1c175f04fe99dfd90c4991176d9
Source dataset
uspto-grants-1995_05
Patent number
US05420343

Reaction notes

Loading…